133528-08-2

Usage

Chemical composition

Consists of a 3,4-dihydroisoquinoline ring with an aniline group and a methyl group attached.

Usage

Commonly used as a building block in the synthesis of various pharmaceuticals and organic compounds.

Unique structure and reactivity

Contributes to its value in the synthesis of complex organic molecules.

Potential medicinal properties

May be utilized in the development of drugs for various therapeutic applications.

Value as intermediate

Often used in the field of organic chemistry for the construction of biologically active compounds.

Upstream product

• 3958-60-9 2-nitrophenylmethyl bromide 
• 88-72-2 1-methyl-2-nitrobenzene 
• 152436-74-3 2-(2-Nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 133527-98-7 5,6,13,13a-tetrahydroisoquino<1,2-b>quinazolinium picrate 

Relevant academic research and scientific papers

Synthesis of [1,2-b] and [2,1-b]Quinazoline Ring Systems via Suitably Substituted α-Cyanoamines

A novel entry into tetrahydro-6H-isoquino[1,2-b]quinazoline and hexahydro-5aH-pyrido[2,1-b]quinazoline ring systems is outlined employing 1,2,3,4-tetrahydroisoquinoline and piperidine as starting material. The anodic cyanation of N-substituted aliphatic amines constitute the key step of the synthesis of the quinazolines 3 and 9.

2-(aminobenzyl)-1,2,3,4-tetrahydroisoquinolines: A new class of α2-adrenergic receptor antagonists

A new class of α2-adrenergic receptor antagonists, the 2-(aminobenzyl)-1,2,3,4-tetrahydroisoquinolines 4 and their derivatives, is described. Two synthetic routes are reported. An investigation of the structure-activity relationships including various substitutions of the isoquinoline moiety and the benzyl group is discussed. The affinity and selectivity for both α1- and α2-adrenoceptors was defined by studying the displacement of [3H]-prazosin (α1-sites) and [3H]-yohimbine (α2-sites) from rat brain membranes. The 2-(2-amino-3,4-dimethoxybenzyl)-6-methoxy-1,2,3,4- tetrahydroisoquinoline 4a presented affinity and selectivity close to yohimbine. In functional experiments the α-adrenoceptor blocking properties of 4a have been evaluated on isolated rat aorta and on the twitch responses of the isolated rat vas deferens.

SYNTHESIS OF ISOQUINOQUINAZOLINES BY CYCLOADDITION REACTION

The cycloaddition reaction of 3,4-dihydroisoquinolinium salts (2c,d) with 2-aminobenzaldehydes (1a,b) was a convenient way to obtain 5,6,13,13a-tetrahydro-8H-isoquinoquinazolinium salts (3a-d).The reduction, transposition and oxidation of these com